Triethylamine → HCID 67235657, compound

HRID 1748305Notes

Reaction equation

HRID 1748305 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:17]=3)[CH:12]=[C:11]2[C:24]([O:26]CC)=O)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+]>C(O)C>[O:26]=[C:24]1[C:11]2=[CH:12][C:13]3[CH:14]=[CH:15][C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][C:18]=3[N:10]2[CH2:9][C:3]2([CH2:4][CH2:5][O:6][CH2:7][CH2:8]2)[CH2:2][NH:1]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 67235165HCID 67235165, compound

Product 1

HCID 67235657HCID 67235657, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the crude diethyl 1-{[4-(aminomethyl)tetrahydro-2H-pyran-4-yl]methyl}-1H-indole-2,6-dicarboxylate from the preceding step in ethanol (800 mL) is added triethylamine (16.16 mL, 115.9 mmol) and K2CO3 (16.1 g, 115.9 mmol). The reaction mixture is heated at 80° C. for 2 h and is cooled to room temperature and stirred for an additional 16 h. The solid K2CO3 is removed by filtration and the filtrate is concentrated. The crude compound is purified by flash column chromatography using 3% methanol in CH2Cl2 to afford the title compound (4.2 g, 30% for 3 steps) as a white solid.

Workup

  1. temperatureis cooled to room temperature
  2. customThe solid K2CO3 is removed by filtration
  3. concentrationthe filtrate is concentrated
  4. customThe crude compound is purified by flash column chromatography

Sources & evidence

ORD record
ord-cf2aa814a1d742eb9a9694a0c4ba5333
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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